In April 1983, long before all that shouting, I had broken the story of Trump’s possible involvement in Lincoln West, though I hesitated to run the piece when Trump told me he was “absolutely not” going to invest in the property. The Lincoln West project came up again in November 1984. Trump had announced that he would be glad to help Ronald Reagan in arms negotiations with the Soviets. He was a deal-maker, right? Sounded like a Page Six item, so Richard Johnson, who worked for me then and later became the editor of the column, arranged to interview Trump. While Johnson was on the phone confirming time and other details, Trump suggested I come to his office as well, because he had never met me in person. Even this was not true—we had met at parties—but no point in arguing. So off we went.

As Johnson asked Trump about the Soviets, I inquired about Lincoln West, the sale of which had not been finalized. Trump said nothing was happening with the property but might be soon. He’d let me know. We left his office feeling confident that we’d lined up one good story and would be given first dibs on another. But the very next day, on the front page of the New York Times, this headline appeared: “TRUMP SET TO BUY LINCOLN WEST SITE.” The story began, “Donald Trump said yesterday that he had an agreement to buy the site of the proposed $1 billion Lincoln West housing and office complex.”

Said yesterday? YESTERDAY!? I knew Trump had a penchant for prevarication, but to lie to my face, when he could have taken any one of several routes around the lie? “I had an arrangement with the Times,” he said when I called to ask why. It was on the phone, so I could not see him, but I’m sure he shrugged. Trump is a big shrugger. In this case, the shrug would have meant, as it often did: Eh, why go to the trouble? I killed the arms negotiation story.

It may have been this lie—or perhaps another; there were so many—that prompted me to call Cohn and suggest he give his client a lesson in media relations. There were rules, I insisted: You could say “no comment” or not return a call, but you could not directly lie, certainly not to someone’s face, and still expect them to continue writing about you. Cohn found this very funny, and told me not to worry, that Trump meant no harm: “He’s just very excitable.”

During the meeting in which he lied to me about Lincoln West, Trump said he didn’t pay much attention to the press. It was of little importance to him. This, mind you, during an interview with two newspaper reporters. A moment later, he pulled open a desk drawer and took out copies of a profile of him that had appeared in the Washington Post. Had we seen it, he wondered?

***

Today, Trump calls reporters “disgusting.” That’s the biggest lie of all. I’d argue that his longest and most intimate relationship is with the media, who offer so many opportunities for him to gaze at the person he loves most. Trump, to his credit, understood early how to harness the explosion of media that started with cable TV in the ’80s and grew exponentially into the digital age. With so many media outlets, all desperate for content, the truth is irrelevant, and even negative attention can serve his purposes. Just give them something—anything—to air or to publish.

As the ’80s progressed, I continued to write about Trump, but with increased skepticism. I grew to dislike him so intensely that I cast a nastier eye on him than I did on other celebrities. It was more than the lying—it was the arrogance that seemed to say, “It’s OK for me to lie because I’M DONALD TRUMP.” Yes, I lost my objectivity. Shame on me. But I’d been following Trump for a long time at that point and knew what I was dealing with. In 1987, after a party to celebrate the publication of Trump’s book The Art of the Deal, Inside New York, the column I edited for New York Newsday, gleefully reported that hardly any real stars attended. “This is a party for aspirers,” we quoted one guest as saying.

Tales From the Tabloids: Six New York writers remember The Donald’s early years in the public eye. (Click to read story.) | Illustrations by Antony Hare

But it was hard to sit back and watch as Trump issued one false pronouncement after another that immediately was accepted as truth. Sure, some media outlets exposed him for what he was—Spy magazine was hilariously relentless in its coverage of the “short-fingered vulgarian”—but many news operations ran verbatim what he told them. For instance, he claimed to have used his stellar deal-making skills to buy the St. Moritz hotel on Central Park South in 1985 for a bargain price of $31 million, dutifully reported by a variety of news outlets. According to a Fortune magazine article four years later, he had paid more than twice that, but, hey, who’s counting?

Not all Trump’s contradictions were quite as consequential. In 1987, sportswriter Mike Lupica, in an Esquire column, quoted Trump calling executives at Gulf & Western, the company that then owned the New York Knicks, “schmucks.” I got an item out of it when Trump vehemently denied saying such a thing, claiming the word “schmuck” was not in his vocabulary. (We now know “schlonged” definitely is.) Lupica just as strongly stood by his story. “I hope this doesn’t mean Donald can’t be president,” he said.

I stopped covering Trump for daily newspapers in the late ’80s, but I could not avoid reading about him. There was the Marla Maples scandal—“Moola,” as Ivana called the woman who broke up her marriage. (So sad. We all thought Donald and Ivana were the perfect couple, united in their love of media attention and peach-colored marble.) Then the divorce, the remarriage, the second remarriage, the financial downturns. But nothing seemed to diminish the public’s fascination with him. After the Marla story broke in February 1990, Trump was on the New York Post’s cover for eight straight days—unheard of at the time.

In late 2004, Vanity Fair published an oral history of Page Six. After it appeared, several former Page Six reporters and editors who had been interviewed for the piece by Frank DiGiacomo gathered at a bar for a celebratory drink. As we sat around reminiscing, in strode Trump, accompanied by Melania Knauss, soon to be the third Mrs. Trump. What in the world is he doing here, I wondered? Doesn’t he have someplace to go? Doesn’t he have any friends? He shook a few hands, and went off into the night. I had not seen him in years, but as usual in encountering Trump, with his overblown gestures and language and hair, I was struck by how clumsy and artificial he always seemed. The Apprentice had premiered earlier in 2004, but Trump had acted like its bombastic lead character for decades.

And as he runs for president now, Trump has found his most appreciative audience not among the East Coast elite, who have always looked down on him, but with the sort of people who think The Bachelor is about romance. (I can’t believe they broke up! They were so much in love!) Trump supporters enjoy his campaign trail reality show because they’re familiar with the posturing and the parlance. They don’t care if it’s one long list of scripted falsehoods—it’s satisfying entertainment, like sitting at home in front of a screen, but with the prospect of the star getting his hands on nuclear weapons.

In the late ’80s, I wrote a book about being a gossip columnist in which I devoted half a chapter to Trump’s fondness for falsehood. And in Vanity Fair’s history of Page Six, I expressed regret about contributing to the creation of the never-ending Trump news cycle. He was, I said, “full of crap 90 percent of the time.” The next quotation in the story came from Trump himself: “I agree with her 100 percent.” I had to admire him for that unusual moment of honesty.